Jamaica may seem like a tough nut to crack. It’s often a cruise ship destination, and most travelers stay in one area (and sometimes even just one resort) for their entire trip. Plenty of travelers return home with an idea of Jamaica that’s limited to the specialties and personalities of just a handful of regions. Like any multifaceted country, Jamaica has its ups and downs, good areas and bad. But stepping out of a resort’s walls is incredibly rewarding in Jamaica, where some of its most oft-visited regions — Montego Bay, Negril, Treasure Beach — are dotted as much with luxe resorts and cliffside mansions as hole-in-the-wall local hangouts. A quick guide to the lay of the land unveils all the cool and laid-back nuances of this island where nature plays a role in all things.
Kingston, the capital of Jamaica, is used as a second-choice airport hub (after Montego Bay) and little else to visitors. It’s filled with consulates, embassies, and tall buildings, and doesn’t really convey the calm, cool, beachside vibe of the rest of the island. That said, any time spent in Kingston should start at Norma’s on the Terrace, which serves authentic and fresh Jamaican cuisine in the historic Devon House. Head to Uptown Kingston to find charming streets lined with restaurants, bars, and boutiques. Just take note: Kingston is the kind of place you’d be wise not to walk around in at night, but during the day it’s a thriving, populated city.
Portland and the Blue Mountains are also home to a distinct vibe from the resort-land of Montego Bay and its surrounds. The Blue Mountains are a hiker’s delight and are famous for the many coffee plantations sitting among their peaks and valleys, most of which offer tours to visitors. The nearby town of Portland is considered one of the most beautiful and somewhat untouched parts of the island. It is also called the "Jerk Capital of Jamaica," because of the innumerable roadside stops for jerk chicken and pork in Boston Bay. (Photo courtesy of Flickr/churl)
Find the rich history andoozing cool of James Bond in Oracabessa, about an hour and a half from Kingston. Now owned by Chris Blackwell, Goldeneye is the former home of Bond scribe Ian Fleming and is now a luxe resort with beach cottages, private villas, locally made Blackwell rum (so named for current owner Chris Blackwell), and freshly caught seafood served at the seaside cool restaurant with bold Jamaican flavors.
Montego Bay is home to Jamaica’s other airport. Two hours from Ocho Rios and less from Negril, it’s much closer than Kingston and is a popular destination for cruise ships and tourists. Nicknamed Mo’Bay, it’s often bustling with tourists making their way to or from resorts in Negril and Ocho Rios. It’s also home to Pelican, an authentic eatery serving classics like ackee and saltfish and conch chowder. Giving Boston Bay’s jerk chicken a run for its money, Mo’Bay’s Pork Pit holds the title of the best jerk in town, the meat cooked over hot coals.
Negril is what we think of when we think of the relaxed, cool, sandy beaches of Jamaica. Its crystal blue coastline is smattered with resorts big and small, deluxe and boutique. Every last activity here has something to do with still somewhat unmanicured nature, whether it’s jet-skiing, river rafting, or hiking. This is where people go to laze on a beach, cold beer or cocktail in hand, eating conch and watching the tide come in. Now for the food — Negril’s resorts, like The Caves and Rock House both boast a number of Jamaican restaurants and beachside bars serving local rum, tropical fruits, and freshly caught fish. But for a real taste of local flavor, head to The Hungry Lion,The Jerk Hut, Coconuts International, and White Sands. We hear Selina’shas the tastiest cup of strong local coffee, so any visitors venturing beyond resort walls for breakfast should be advised to stop there. (Photo courtesy of Flickr/samekh9393)
Treasure Beach is on Jamaica’s oft-skipped South shore, where the sand isn’t quite as bright and the coastline has significantly fewer big resorts. But not including it would be to leave out one of the country’s coolest, rugged-meets-luxury resorts that serves mouthwatering, authentic cuisine everyday — Jakes. Try Jamaica’s national dish (ackee and saltfish) there, sample fresh seafood and pizza at Jack Sprat on the property, or hit up the hotel-recommended (and local-approved) Little Ochie for fresh lobster, crab, and a strong cocktail all served under a thatched roof.